Lent: Prayer Penance and Almsgiving – Lent 2021


In this talk, Jon discusses Prayer, Penance, and Almsgiving. He shares his personal Lenten resolutions and gives insights and ideas on what we can do to try and have a more meaningful Lenten season.

Thank you for watching and participating in this retreat!

Not Registered, yet? Don’t miss the rest of the talks! Register for the Pray More Retreat! 


Audio MP3

Click here to download audio file.

Printable Study Guide PDF

Click here to download the printable study guide.

Printable Transcript PDF

Click here to download the transcript of the video presentation.

Reflective Study Guide Questions

“And the king will say to them in reply, ‘Amen, I say to you, whatever you did for one of these least brothers of mine, you did for me.’”

Matthew 25:40

1. Jon emphasizes the importance of prayer as the foundation for living the Christian life. What does your prayer life typically look like at this point in your life? Where do you see room for improvement? 

2. Establishing a strong prayer life and relationship with God is less about discovering where we can fit God into our day and more about discerning how God wants us to connect with Him. How might God be calling you to connect with Him more deeply this Lent? 

3. Practices of penance, both during Lent and at all points in our lives, should have the goal of helping us let go of things that are interfering in our relationship with God or our pursuit of virtue. What are some areas in your life where you should consider working on sacrifice for the sake of holiness?

4. Jon says that almsgiving is a practical way in which we can live out the surge of the heart that prayer is. How can you work on entering into almsgiving more deeply, so that it becomes a way to live out your love for God?

Text: Prayer Penance and Almsgiving

Hey everybody, Jon Leonetti here, and we are back for another Pray More Novenas, Lenten Retreat. And I’m excited to be asked to do this again, this is always a highlight. I think it’s been like three times now, which is pretty awesome, giving a few talks here. So, I hope you enjoy them. This one, going to be talking about prayer, penance and almsgiving. But, without it lets pray, without doing this next part, all the other parts are void. So, let’s pray.

Opening Prayer

In the name of the Father, of the Son and of the Holy Spirit, Amen. The judgment of nations. Now listen real closely. “When the son of man comes in His glory and all the angels with Him, will sit upon His glorious throne, imagine that. And all the nations will be assembled before Him. And He will separate them one from another as a shepherd separates the sheep from the goats. He will place the sheep on His right and the goats on His left.

Then the King will say to those on His right, ‘Come you who are blessed by my father, inherit the kingdom prepared for you from the foundation of the world. For I was hungry, and you gave me food. I was thirsty and you gave me drink. A stranger and you welcomed me. Naked and you clothed me. Ill and you cared for me. In prison and you visited me.’ Then the righteous will answer him and say, ‘Lord when did we see you hungry and feed you or thirsty and give you drink? When did we see you a stranger and welcome you? Or naked and clothed you? When did we see you ill or in prison and visit you?’ And the King will say to them and reply, ‘Amen I say to you, whatever you did for one of these least brothers of mine, you did it for me.’

Then He will say to those on the left, ‘Depart from me, you are cursed into the eternal fire prepared for the devil and his angels. For I was hungry, and you gave me no food. I was thirsty and you gave me no drink. A stranger and you gave me no welcome. Naked and you gave me no clothing. Ill and in prison and you did not care for me.’ Then they will answer and say, ‘Lord, when did we see you hungry, or thirsty, or naked, or a stranger, or ill, or in prison and not minister to your needs?’ He will answer them, ‘Amen I say to you, what you did not do for one of these least ones, you did not do for me.’ And these will go off to eternal punishment, but the righteous to eternal life.” Lord bless this time we have together. Send your Holy Spirit upon all of us, so that we may do your will. Amen. In the name of the father and of the son and of the Holy Spirit, Amen.

Mother Theresa says, “You want to summarize the gospel in five words? You did it to me.” Five words. You want to summarize the entirety of the gospel, of the Christian life, right there. You did it to me. And I think it’s really kind of a perfect lead in here for what we’re talking about in this talk, prayer, penance and almsgiving. And I think most especially the almsgiving part, but we can try to fit some of the prayer, the penance part in it as well. because we take care of ourselves, we are bears of Jesus Christ into the earth. And so far, as we take care of ourselves as well in the proper ways in prayer and relationship with God, we’re doing what God asks of us to. And so, I’m going to start kind of like, and go through prayer, penance and almsgiving and kind of what they are individually, but I think there’s a tie in as well. And we’ll kind of do that at the end and kind of tie in all of this together.

And you’ll notice I have some of my notes here, so if I’m like looking down at my computer, you’ll see that I have some especially saint quotes. Those that know me or that have been, you know, a part of these talks now for the last few years, maybe even longer than that, you know that I absolutely love the saints. The lives, teachings and wisdom of them, is something that I try to read on a regular basis. And so, I can’t help but talk, in any of my talks, without at least quoting them once in a while. Already did that with Saint Teresa of Calcutta.

Faith and Prayer

But we’ll talk about prayer. I have a saying that I say oftentimes. And the saying goes like this, “Faith without prayer is a hobby.” Again, if you’ve heard me speak, you’ve probably heard me say that. “Faith without prayer is a hobby.” And one of the things I love about Lent, one of the things I really love about Lent, is it really does a good job, the season, of refocusing us on that for which is most important, and that is our prayer lives.

Because Christianity goes beyond just doing good things. Goes beyond it. Where it starts is in relationship to God. You see, Jesus in this parable doesn’t say, “Just go do good things for other people.” He says, “That for what you do for them, you did for me.” There’s a relational aspect there, that God calls us to. In both Word and our hearts and in our deeds. So that in so far as I am doing good, it’s kind of the gasoline to the tank, prayer is. The engine doesn’t run, the virtue doesn’t grow in order for me to venture outside of myself, if I first don’t have that relationship with God. That’s why we mentioned prayer first, it’s the foundational piece. And it’s that for which launches us out into, clothing the naked and feeding the hungry and giving drink to the thirsty.

You know, Saint Teresa of Calcutta, she was once scolded by someone that said that she prayed too much. And they told her, they said, “Think of how many more people you could go out and help, if you didn’t have so many hours of prayer in the morning and in the evening.” Imagine scolding Mother Theresa by the way. And Mother Teresa looked at this person and she said, “I wouldn’t be able to help anyone, if it wasn’t for that time and prayer.” So again, that analogy of the gasoline to the tank? The engine doesn’t move without it, Mother Teresa embodied that. She understood first and foremost, where the grace, the strength, that she was to be able to live the virtuous life, to live holiness was to come from. And that was not on her own accord.

The Catholic Mass

All this grace, Saint Paul tells us, it’s dependent on God. And so, what prayer does, is it really kind of hones us in to be able to open up ourselves, the floodgates, for God to be able to pour Himself in, to give us Himself. And there’s really kind of, you know, of course, different dimensions to prayer. So, when we talk about like the Church’s prayer, the highest prayer, the best prayer, if you will, the most perfect prayer, is that of the Holy Mass. And that is something that we share in community. So that’s something for all of us. The Holy Sacrifice of the Mass, what we call really heaven on earth. You know, I heard it once said that if you’re bored at mass, you’re going to be bored in heaven. Think about that. If you’re bored at mass, you’re going to be bored in heaven. We say mass, the Holy Mass, is heaven on earth. And so, if we’re bored there, we’re certainly going to be bored in heaven. The mass is where heaven touches down to earth and earth is lifted up to heaven.

See, I don’t think it’s because we’re bored at what’s actually happening at the mass. Because what’s actually happening at the mass, if we were actually able to see it, would stop our hearts, we wouldn’t be able to take it. It’s just that we don’t know. And there maybe some of us, you know, haven’t really kind of, and I say like, if we really knew what was happening, right? If we were really to see it, our human hearts and minds wouldn’t be able to take it. But we can educate ourselves on what’s actually happening at the mass. Many of the saints tell us what’s happening. You know, here we are at Calvary. We are here at the foot of the cross. And God isn’t giving us just a special gift or a special grace, He’s given us Himself. You know, Saint John Vianney said that “If God wanted to give us any more in the Holy Mass, He couldn’t. Because He’s already given us everything. He’s given us Himself.” God gives us Himself at the mass, there is that relationship right there. I mean, that is prayer par excellence.

Different Types of Catholic Devotions

Of course, there’s different devotions then that the church calls us to. And we would say these are more like private devotions, right? Like the Rosary would be considered a private devotion. I think it’s a pretty big one. And, you know, most saints when you read their lives, they’re flipping the beads a lot. But it is not necessary for us, or for every single person, to pray the Rosary in order to get to heaven, as we know. I think it’s pretty helpful, I think it’s the most powerful prayer outside of the Holy Mass for us, as Catholics, but it is a private prayer and the same thing for different devotions as well.

What your private prayer looks like, is going to be between you and our Lord. And that’s where we go to prayer and we kind of form that, what that relationship looks like. And how does it, we nurture that relationship with prayer with God. If you haven’t done that yet, if you haven’t really kind of found a way of prayer, I want to challenge you, this Lent, to do that. And maybe that means praying a decade of the Rosary. And really seeing is this where the Lord is calling you, to be a man or a woman of the Rosary now, in your private prayer.

Adoration, The Divine Mercy Chaplet. Every day at three o’clock, I have a friend that stops what she’s doing every day at three o’clock with her family, and she prays the Divine Mercy Chaplet. Every single day, 365 days a year. Think of that kind of commitment. And she’s in a meeting or something happens there, or a doctor’s appointment, she’ll pray it right before or right after. How beautiful is that? And she’s kind of allowed her day to pattern a prayer. You know, I’ve heard it once said that we don’t want to fit God into our day, we want to fit our day into God. That’s the Christian life. And so, to be able to make that time with God, this Lent, and really tried to figure out a pattern of prayer, I think it’d be a big challenge for every one of us. Where’s does the Lord really speak to us? For me, I love reading sacred scripture. And reading it, I love using my imagination, kind of Lectio Divina, as it would otherwise traditionally be called, but putting myself in the story. It’s a way in which I’m really connected with our Lord. And He’s able to really kind of show me things, not visions or anything like that, but in the story, in my imagination, in my heart, be able to show me things and open up those graces, those areas that I need to invite Him in. It’s a powerful way for me to pray.

My family, we’ve really grown a liking to the Liturgy of the Hours, and we don’t pray them all day every day, but one of the things that we like to do is night prayer. It’s a good time for us to make an examination of conscience. That’s kind of become a pattern in our family, a habit of prayer. And again, we don’t make it every night, but many nights we do. And that’s a staple for the Leonetti household. But whatever way, I’m asking you this Lent, to be able to make that time, and that’s how prayer is spelled by the way, T-I- M- E, but to make that time to create a pattern of prayer. And not just for Lent, but to do so beyond.

The Sin of Pride

You know, lent again, it’s a launching pad, it’s a time for us to really again get serious about this whole thing. And then hopefully, move us in the form of direction of where it is and how it is, we should be living. So that’s prayer. Number two penance. Now, again, there’s two kind of components to this and I want to really kind of speak to both. One is sacramentally. So, we talk about the Sacrament of Penance or the Sacrament of Confession or Reconciliation. A sacrament with three names to it, pick whichever one you want. Lent is a good time for us to be renewed in this grace as well, this gift. I think it’s the second most powerful sacrament to combat the world’s worst sin.

What’s the world’s worst sin? Pride. Pride is the base of which all sin comes from. You name any kind of sin and it all comes back to pride. “What it is that I think, what it is that I want.” It all comes back to the ego; all comes back to “me”. So, great way to break that, first and foremost, is to allow the Sacrament of Reconciliation to have a place in our life. And again, not just going once a year during Lent, or once a year during Advent or the Easter season, you know? I’ve always said, try cleaning your house once a year. It’s not going to look too great by the end, right? But we go to confession as often as we need, maybe every four weeks, every six weeks, or every couple of months or maybe once a quarter, to be able to ask our Lord back into our life again in the times that we’ve separated ourselves from Him.

So, confession is a beautiful opportunity in the life of the Church to be able to hear those saving words, what we call absolution. Where the priest standing in for Christ Jesus, and they represented it of Jesus. And when he’s ordained, we have to remember, he is now able with authority, to act in what the Church calls, “In persona Christi capitis,” and the very person of Jesus Christ, the head. This is why He speaks in the first person; this is why our Lord speaks in the first person when He speaks to us and giving us absolution through the priest. The priest says, “I absolve you of your sins in the name of the father and of the son and of the Holy Spirit.” Is that the priest speaking? It’s Jesus. “I absolve you,” through His authority.

That’s why the priest wears the stole that symbolizes his authority by God, to absolve us of our sins. And why would we not take advantage of that? Jesus says to His apostles after he Rose from the dead, “Those that here you hear me.” And the apostles knew what that meant. They were to go now and forgive sins. And those sins they forgave were forgiven, those sins they retained, were retained, see the authority here? God gives us priestly authority. But we have to be willing to allow them to exercise that. And that doesn’t happen if we don’t show up. And I think that’s one of the biggest tragedies in the Church today. I think one of the biggest tragedies in our Church today is a shortened confession line. Many of us have lost that. And the basics, right? Of the faith that sometimes we try to overcomplicate, the confession, reconciliation, penance. But then there’s also another component to it, I want to kind of read something here.

Blissful Penance

Saint Peter of Alcantara, he said this, he said, “Oh, blissful penance which has purchased for me so great a reward.” Now, I remember watching the Olympics, I think it was a couple of years ago, whenever they were. And, or maybe longer than that now. But anyway, I remember watching them and a woman won a gold medal in skiing. I couldn’t say who this is, I don’t remember. But I remember when they interviewed her right afterwards, they put the microphone in her face and they said, “You just won the gold medal, how do you feel?” And she was just going crazy. And she said, “I’m going to get to have ice cream tonight.” And I thought, “That’s a strange answer.” “I’m going to get to have ice cream tonight,” she said. She deprived herself for the last four years of ice cream, so that she could win this award, to try and get in the best shape she possibly could. And she knew that she was going to have to cut out some of those things in her life that were going to get in the way of that. And she won the race. She won the prize, the gold medal.

See here again, thinking these terms, Saint Peter of Alcantara, he said, “Oh blissful penance, which has purchased for me so great a reward.” And what are those things in our life that are getting in the way? What are those things we can sacrifice now? And sacrifice, it’s the name of the game, right? It’s what love is ultimately. Sacrificial love does so in penance. What are those things we need to now move away? Lent’s a really good time to zero in on those things. And we talk about giving things up for Lent or taking things on.

But I always I was encouraged people, the people that come to me and say, “Oh, I’m just going to do this instead of, you know, giving something up.” I always encourage people to also give something up. You know, I remember when I got married to my wife, when she converted to Catholicism, she didn’t quite know how this like Lent thing goes, and it was the first year of our marriage. And she says, “I’m going to give up chocolate for Lent.” And I was like, “My wife hates chocolate, right? It doesn’t make any sense. No, it’s got to hurt a little bit.” It’s got to remind us of what it is that we’re all about. That reminder there.

So, prayer, of course, the highest form of prayer is a Holy Sacrifice of the Mass. And then of course, we have our private prayer. It really cultivated a renewed sense of prayer with our Lord, relationship with our Lord. Repentance, of course sacramentally, we have penance in the Sacrament of Reconciliation, confession, penance. But also, living that kind of ongoing penance in our life, doing our best to really kind of, again, examine our conscience to see what is getting

in the way of our Lord in my life? What are those things that I need to let go of? God asks us to do that and to live in that kind of penance on a regular basis, not to be miserable, but it frees us, that’s ultimately what penance does.

Now you here see Peter there, “Oh, blissful penance,” right? It’s redemptive in a way, suffering can be redemptive. I’m going to talk about that again. But this redemption through penance that our Lord offers us, so needed I think in our world today, especially a consumeristic world. And that kind of leads us right into, speaking of consumerism, it leads us right into almsgiving.

Live Generously

Now our Holy Father, Pope Francis, said that, “The world today and the reason why so many are miserable in our world, is because what we’ve done is turn inward on ourselves.” We’ve made our lives all about, me. And the reason why it makes us miserable when that happens, is because that’s not how we were built, that’s not how we were created to live. Now Saint Thérèse of Lisieux, says, “That prayer is a surge of the heart”, there’s the way to live. “A surge of the heart”. It’s an outward, gift of self, kind of a reaching to God. Think of that as meditation. Contemplation is God reaching back down to us. But to live our lives with that kind of surge of a heart, not turning inward on myself, or my life’s just all about me. And almsgiving is an opportunity to be able to live that day in and day out. That gift of what? Myself, for the other, for their own sake. Again, what love is. That sacrificial gift where my life isn’t just all about me.

So, what are some ways that we can do that? You’ve heard the traditional time, talent, treasure? Great. But oftentimes I find that the people that are saying that aren’t the ones actually trying to get intentional on doing it. I remember a woman came up to me once she said, “Jon, one of the ways that I give of myself to my parents, is I give money.” And I said, “Great.” And she said, “Dumb, it just makes me feel good to do so.” And I said, “Well then you’re probably not giving enough money.” I remember she’s kind of stared at me. Almsgiving in a way, is a sacrifice, and we should feel that a little bit. We’re not going to put ourselves, you know, in financial insecurity or to put ourselves, you know, be irresponsible for our families. No, no one’s asking us to do that. But to feel that, that sacrificial gift for a parish, for someone in need, and be able to look for more ways to be able to do that.

You know, 2021 for me during the New Year, I kind of deemed this a year of generosity for myself. As I want to become more generous over the course of the next year. But God is calling all of us too. And that doesn’t mean I’m going to be able to cover all of these things that our Lord asks us to cover, I’m just one person. But maybe parking myself in one or two or three areas, being attentive to those needs of others or communities, my parish, or the needs, is the way in which God calls us to reorder our life. We do it imperfectly friends, every one of us, and we’re not going to do it perfect. And don’t get too frustrated with yourself, God’s mercy is abundant in this. But it’s so important for us to be able to learn and relearn especially during this Lenten season. Have a prayerful Have a forgiving? Yeah, I guess we’ll say that. And have an almsgiving Lent, everyone. God bless you, thanks for having me.

About Jon Leonetti

Jon Leonetti is a nationally known Catholic speaker, best-selling author and radio host who conveys a message of lasting fulfillment in Jesus Christ. Through Jon’s keynote presentations and parish missions, thousands of Catholics each year discover the freedom Christ offers by way of his life and love.

Jon is the founder of SanctifyU, a first of its kind membership platform on the lives, teachings, and wisdom of the saints. Jon is the author of five books, including Mission Of The Family, Your God Is Too Boring and, The Art of Getting Over Yourself: And Why You’ll Be Happier When You Do. Jon’s first two books are published and featured in Matthew Kelly’s Dynamic Catholic Book Program. Jon’s writings, talks, and programs have been endorsed by Archbishop Joseph Kurtz, New York Times Bestselling author Immaculee Ilibagiza, Mark Hart, Chris Stefanick, Jennifer Fulwiler, Brandon Vogt and more. 

Jon believes that our deepest longing for happiness and wholeness is fulfilled in the encounter with Jesus Christ. Through prayer, the Sacraments, family life, and the help of Mary and the saints, Jon wants to cultivate an intimate relationship with Jesus, and help others do the same. With this message Jon has been featured and interviewed by the nation’s top Catholic websites, blogs, and radio shows, helping Catholics in all walks of life to fall in love and stay in love with the living God.

At home, Jon enjoys reading, sports, exercising, coffee and, most of all, spending time with his wife Teresa and their children. Jon has a masters degree in moral theology.​​  You can learn more about Jon here.